Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
  • C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
  • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
  • G03F7/094—Multilayer resist systems, e.g. planarising layers
• • G—PHYSICS
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  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
  • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
  • G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
  • C08G59/22—Di-epoxy compounds
  • C08G59/24—Di-epoxy compounds carbocyclic
  • C08G59/245—Di-epoxy compounds carbocyclic aromatic
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  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
  • C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
  • C08G59/4207—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof aliphatic
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
  • C08K5/092—Polycarboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L101/00—Compositions of unspecified macromolecular compounds
  • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
  • C08L101/06—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L101/00—Compositions of unspecified macromolecular compounds
  • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
  • C08L101/06—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing oxygen atoms
  • C08L101/08—Carboxyl groups
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
  • C09D7/40—Additives
  • C09D7/60—Additives non-macromolecular
  • C09D7/63—Additives non-macromolecular organic
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
  • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
  • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
  • H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
  • H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
  • H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
  • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
  • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
  • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
  • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
  • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
  • H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
  • H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
  • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
  • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
  • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
  • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
  • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
  • H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
  • H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
  • H01L21/30604—Chemical etching
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
  • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
  • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
  • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
  • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
  • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
  • H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
  • H01L21/3205—Deposition of non-insulating-, e.g. conductive- or resistive-, layers on insulating layers; After-treatment of these layers
  • H01L21/321—After treatment
  • H01L21/3213—Physical or chemical etching of the layers, e.g. to produce a patterned layer from a pre-deposited extensive layer
  • H01L21/32133—Physical or chemical etching of the layers, e.g. to produce a patterned layer from a pre-deposited extensive layer by chemical means only
  • H01L21/32134—Physical or chemical etching of the layers, e.g. to produce a patterned layer from a pre-deposited extensive layer by chemical means only by liquid etching only
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
  • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
  • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
  • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
  • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
  • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
  • H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
  • H01L21/3205—Deposition of non-insulating-, e.g. conductive- or resistive-, layers on insulating layers; After-treatment of these layers
  • H01L21/321—After treatment
  • H01L21/3213—Physical or chemical etching of the layers, e.g. to produce a patterned layer from a pre-deposited extensive layer
  • H01L21/32139—Physical or chemical etching of the layers, e.g. to produce a patterned layer from a pre-deposited extensive layer using masks
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/16—Coating processes; Apparatus therefor
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/20—Exposure; Apparatus therefor
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/26—Processing photosensitive materials; Apparatus therefor
  • G03F7/30—Imagewise removal using liquid means
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
  • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
  • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
  • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
  • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
  • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
  • H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
  • H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
  • H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
  • H01L21/3081—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their composition, e.g. multilayer masks, materials
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
  • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
  • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
  • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
  • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
  • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
  • H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
  • H01L21/3105—After-treatment
  • H01L21/311—Etching the insulating layers by chemical or physical means
  • H01L21/31144—Etching the insulating layers by chemical or physical means using masks

Definitions

• the present invention relates to a composition forming a protective film having excellent resistance particularly to a wet etching liquid for semiconductor, in a lithography process in the production of a semiconductor.
• the present invention relates to a method for producing a substrate having a resist pattern to which the protective film is applied, and a method for producing a semiconductor device.
• Patent Literatures 1 and 2 disclose a protective film forming composition comprising a specific compound against aqueous hydrogen peroxide solution.
• Patent Literature 1 WO 2018/052130 A1
• Patent Literature 2 WO 2018/203464 A1
• the resist underlying film is required to have a good masking function (i.e., the masked part can protect the substrate) against wet etching liquid used during the processing of the base substrate.
• the resist underlying film is used as a protective film of a substrate.
• a protective film with fast etching speed (high etching rate) that permits swift removal by dry etching is looked for so that the base substrate would not be damaged.
• An object of the present invention is to solve the above-mentioned problems.
• the present invention includes the followings:
• a protective film forming composition against a wet etching liquid for semiconductor comprising: (A) a compound comprising at least 3 carboxyl groups; (B) a resin or monomer, and a solvent.
• X is a divalent organic group selected from a direct bond, —CH 2 —, —C(CH 3 ) 2 —, —CO—, —SO 2 — and —C(CF 3 ) 2 —; each of R 1 and R 2 independently represents a monovalent organic group selected from an alkyl group having 1 to 4 carbon atoms, a hydroxy group, a cyano group, a nitro group, a halogen atom, and an alkoxy group having 1 to 4 carbon atoms; each of n 1 and n 2 independently represents an integer of 1 to 9, wherein n 1 +n 2 is an integer of 3 to 10; and each of m 1 and m 2 independently represents an integer of 0 to 7, wherein m 1 +m 2 is an integer of 0 to 7; or the compound comprising at least 3 carboxyl groups (A) is selected from (i) the compound wherein the aromatic ring having 6 to 40 carbon atoms is benzene or naphthalene, and
• X is a divalent organic group selected from a direct bond, —CH 2 —, —C(CH 3 ) 2 —, —CO——SO 2 — and —C(CF 3 ) 2 —; each of R 1 and R 2 independently represents a monovalent organic group selected from an alkyl group having 1 to 4 carbon atoms, a hydroxy group, a cyano group, a nitro group, a halogen atom, and an alkoxy group having 1 to 4 carbon atoms; each of n 1 and n 2 independently represents an integer of 1 to 9, wherein n 1 +n 2 is an integer of 3 to 10; and each of m 1 and m 2 independently represents an integer of 0 to 7, wherein m 1 +m 2 is an integer of 0 to 7.
• a method for producing a substrate having a resist pattern comprising the steps of:
• the substrate having a resist pattern is for manufacturing a semiconductor.
• a method for producing a semiconductor device comprising the steps of:
• the protective film forming composition of the present invention is required to have the following properties in good balance, for example, in the lithography process in the semiconductor production: (1) Good masking function against wet etching liquid used during the processing of the base substrate; (2) High dry etching rate, and (3) Superior flattening effect to a stepped substrate.
• the well-balanced performance of these properties (1)-(3) facilitates micro fabrication of semiconductor substrates.
• the protective film forming composition of the present application is a protective film forming composition against a wet etching liquid for semiconductor comprising:
• the compound comprising at least 3 or more carboxyl groups (A) preferably comprises 3 to 6 carboxyl groups, and more preferably, comprises 3 or 4 carboxyl groups.
• the compound comprising at least 3 or more carboxyl groups (A) preferably has a ring structure.
• the ring structure is preferably selected from an aromatic ring having 6 to 40 carbon atoms, an aliphatic ring having 3 to 10 carbon atoms, and a heterocyclic ring.
• the “aromatic ring having 6 to 40 carbon atom” includes benzene, naphthalene, anthracene, acenaphthene, fluorene, triphenylene, phenalene, phenanthrene, indene, indane, indacene, pyrene, chrysene, perylene, naphthacene, pentacene, coronene, heptacene, benzo[a]anthracene, dibenzophenanthrene, dibenzo[a,j]anthracene, and the like.
• the “aliphatic ring having 3 to 10 carbon atoms” includes cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, spirobicyclopentane, bicyclo[2.1.0]pentane, bicyclo[3.2.1]octane, tricyclo[3.2.1.02,7]octane, spiro[3,4] octane, and the like.
• the aromatic ring having 6 to 40 carbon atoms is selected from benzene and naphthalene, or the compound (A) is preferably selected from the compound represented by formula (1):
• X is a divalent organic group selected from a direct bond, —CH 2 —, —C(CH 3 ) 2 —, —CO—, —SO 2 — and —C(CF 3 ) 2 —; each of R 1 and R 2 independently represents a monovalent organic group selected from an alkyl group having 1 to 4 carbon atoms, a hydroxy group, a cyano group, a nitro group, a halogen atom, and an alkoxy group having 1 to 4 carbon atoms; each of n 1 and n 2 independently represents an integer of 1 to 9, wherein n 1 +n 2 is an integer of 3 to 10; and each of m 1 and m 2 independently represents an integer of 0 to 7, wherein m 1 +m 2 is an integer of 0 to 7.
• alkyl groups having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a cyclopropyl group, an n-butyl group, an i-butyl group, an s-butyl group, a t-butyl group, a cyclobutyl group, a 1-methyl-cyclopropyl group, and a 2-methyl-cyclopropyl group.
• alkoxy groups having 1 to 4 carbon atoms include a methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, s-butoxy group, and t-butoxy group.
• heterocyclic ring examples include furan, pyrrole, pyran, imidazole, pyrazole, oxazole, thiophene, thiazole, thiadiazole, imidazolidine, thiazolidine, imidazoline, dioxane, morpholine, diazine, thiazine, triazole, tetrazole, dioxolane, pyridazine, pyrimidine, pyrazine, piperidine, piperazine, indole, purine, quinoline, isoquinoline, quinuclidine, chromene, thianthrene, phenothiazine, phenoxazine, xanthene, acridine, phenazine, carbazole and triazine.
• the triazine may be a compound comprising triazineone, triazinedione, or triazinetrione; however, a compound comprising triazinetrione is preferred.
• Examples of compounds having at least 3 or more carboxyl groups in the present application may include the following formulae (A-1) to (A-25), for example, but are not limited thereto.
• the protective film forming composition of the present invention includes (B) a resin or monomer, as an essential component.
• a polymer with a weight average molecular weight of more than 1,000 may be used.
• the polymer include, without being particularly limited, polyester, polyether, polyether ether ketone, polyamide, polyimide, novolac resin, maleimide resin, acrylic resin and methacrylic resin.
• the upper limit of the weight average molecular weight of the polymer is, for example, 100,000 or 50,000.
• the resin preferably has at least one or more hydroxy group in its unit structure.
• Examples of the resin having at least one or more hydroxy group in the unit structure may include, for example, a resin having a unit structure of the below-mentioned (2), which is a reaction product (B1) of a diepoxy compound (C) and a bi- or more functional proton generating compound (D).
• a resin having a unit structure of the below-mentioned (2) which is a reaction product (B1) of a diepoxy compound (C) and a bi- or more functional proton generating compound (D).
• the reaction product may include a unit structure represented by the following formula (2):
• each of R 3 , R 4 , R 5 , R 6 , R 7 and R 8 independently represents a hydrogen atom, methyl group, or ethyl group;
• Q 1 represents a divalent organic group between two carbon atoms; and each of m 3 and m 4 independently represents 0 or 1.
• Q 1 in formula (2) may be represented by the following formula (3):
• Q 2 represents a direct bond, or a divalent organic group having at least one alkylene group having 1 to 10 carbon atoms that may be interrupted by —O—, —S—, or —S—S—, an alkenylene group having 2 to 6 carbon atoms, an alicyclic hydrocarbon ring having 3 to 10 carbon atoms or an aromatic hydrocarbon ring having 6 to 14 carbon atoms; and the divalent organic group may be substituted with at least one group selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a halogen atom, a hydroxy group, a nitro group, a cyano group, a methylidene group, an alkoxy group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 1 to 6 carbon atoms, and an alkylthio group having 1 to 6
• Q 1 in formula (2) may be represented by the following formula (4):
• Q 3 represents the following formula (5), (6), or (7).
• each of R 9 , R 10 , R 11 , R 12 and R 13 independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, a benzyl group, or a phenyl group; and the phenyl group may be substituted with at least one radical selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkoxy group having 1 to 6 carbon atoms, and an alkylthio group having 1 to 6 carbon atoms; and R 11 and R 12 may bond to each other and may form a ring having 3 to 6 carbon atoms.
• diepoxy compound (C) forming a structural unit represented by formula (2), in which m 3 and m 4 represent 1, include compounds having diglycidyl ether and diglycidyl ester having two epoxy groups represented by the following formulae (C-1) to (C-51), but are not limited to these examples.
• Examples of a bi- or more functional proton generating compound (D) forming a structural unit represented by formula (2), in which m 3 and m 4 represent 0, include compounds represented by the following formulae (D-1) to (D-47), which have two carboxyl groups, hydroxyphenyl groups, or imide groups, and acid dianhydrides, but are not limited to these examples.
• Examples of the unit structure of the reaction product (B1) of the diepoxy compound (C) and the bi- or more functional proton generating compound (D) include the following formulae (B1-1) to (B1-38), but are not limited to these examples.
• the resin having at least one hydroxy group in the unit structure may be a resin having, at a terminal, a structure containing at least one set of two hydroxy groups adjacent to each other in the molecule.
• the structure containing at least one set of two hydroxyl groups adjacent to each other in the molecule may be a 1,2-ethanediol structure.
• the 1,2-ethanediol structure may include a structure represented by the following formula (8):
• X represents any of —COO—, —O—, —S—, or —NR 17 — and R 17 represents a hydrogen atom or a methyl group.
• Y represents an alkylene group having 1 to 4 carbon atoms optionally being substituted.
• R 14 , R 15 and R 16 represents a hydrogen atom, or an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 40 carbon atoms, each of the groups optionally being substituted, and R 14 may form a ring together with R 15 or R 16 .
• R 14 forming a ring together with R 15 or R 16 include cyclopentane, cyclohexane, and bicyclo[2,2,1]heptane.
• the ring is induced by, for example, allowing a compound such as cyclopentane-1,2-diol, cyclohexane-1,2-diol, and bicyclo[2,2,1]heptane-1,2-diol, to react with a polymer end.
• a compound such as cyclopentane-1,2-diol, cyclohexane-1,2-diol, and bicyclo[2,2,1]heptane-1,2-diol
• R 14 , R 15 and R 16 may be a hydrogen atom.
• Y may be a methylene group.
• X may be —S—.
• Examples of compounds that form the polymer end having a 1,2-ethanediol structure include compounds represented by the following formulae (E-1) to (E-4).
• examples of structures that form the polymer end having a 1,2-ethanediol structure include compounds represented by the following formulae (B 1-39) to (B 1-50), but are not limited to these examples.
• Monomers with a molecular weight of 1,000 or less can be used as the monomers.
• the molecular weight of the monomer is preferably within the range of 200 to 1,000 and more preferably 500 to 1,000.
• the monomer preferably has at least one hydroxy group in the molecule.
• Examples of the monomer (B2) having at least one hydroxy group in the molecule may include the following formulae (B2-1) to (B2-8), but are not limited these examples.
• the monomer (B2) having at least one hydroxy group in the molecule for example, can be obtained by the reaction of a polyfunctional epoxy compound with a proton generating compound.
• the protective film forming composition of the present invention may be prepared by dissolving the above-mentioned components in an organic solvent, and the composition is used in a uniform solution state.
• the solvent for the protective film forming composition of the present invention there is no particular limitation as long as it is a solvent that can dissolve the (B) resin or monomer, and any of such solvents may be used.
• the protective film forming composition of the present invention is used in a uniform solution state, and therefore, taking the application properties of the composition into consideration, it is recommended that a solvent generally used in a lithography process be used.
• organic solvents examples include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate, toluene, xylene, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, cycloheptanone, 4-methyl-2-pentanol, methyl 2-hydroxyisobutyrate, ethyl 2-hydroxyisobutyrate, ethyl ethoxyacetate, 2-hydroxyethyl acetate, methyl 3-methoxypropionate, ethyl 3-
• propylene glycol monomethyl ether preferred are propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, ethyl lactate, butyl lactate, and cyclohexanone.
• propylene glycol monomethyl ether and propylene glycol monomethyl ether acetate are especially preferred.
• the resist underlying film forming composition of the present invention may contain a cross-linking agent component.
• the cross-linking agents include those of melamine, substituted urea, or polymers of these.
• Preferred is a cross-linking agent having at least two cross-linking forming substituents, and examples include compounds, such as methoxymethylated glycoluril, butoxymethylated glycoluril, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzoguanamine, butoxymethylated benzoguanamine, methoxymethylated urea, butoxymethylated urea, methoxymethylated thiourea, and methoxymethylated thiourea. Further, a condensation product of these compounds may be used.
• a cross-linking agent having a high heat resistance may be used.
• a compound containing in the molecule thereof, a cross-linking forming substituent having an aromatic ring for example, a benzene ring or a naphthalene ring
• an aromatic ring for example, a benzene ring or a naphthalene ring
• Examples of the compounds include compounds having a partial structure of formula (2-1) below, and polymers or oligomers having a repeating unit of formula (2-2) below.
• R 18 , R 19 , R 20 , and R 21 are a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and those mentioned above as examples may be used as these alkyl groups.
• n 3 satisfies 1 ⁇ n 3 ⁇ 6-n 4
• n 4 satisfies 1 ⁇ n 4 ⁇ 5
• n 5 satisfies 1 ⁇ n 5 ⁇ 4-n 6
• n 6 satisfies 1 ⁇ n 6 ⁇ 3.
• the above-mentioned compounds are available as products of Asahi Yukizai Corporation and Honshu Chemical Industry Co., Ltd.
• the compound of formula (2-15) is available under the trade name: TMOM-BP, manufactured by Asahi Yukizai Corporation.
• the amount of cross-linking agent added varies depending on the coating solvent used, the base substrate used, the required solution viscosity, the required film shape, and others. However, it is generally within the range of from 0.001 to 80% by mass, preferably from 0.01 to 50% by mass, and even more preferably from 0.1 to 40% by mass based on the total solid content of the protective film forming composition.
• These cross-linking agents may cause cross-linking reactions by self-condensation.
• the cross-linking agents can cause cross-linking reaction with those cross-linkable substituents.
• the protective film forming composition of the present invention may contain, as an optional component, a cross-linking catalyst for accelerating the cross-linking reaction.
• a cross-linking catalyst for accelerating the cross-linking reaction.
• an acidic compound, a basic compound, or a compound capable of generating an acid or a base due to heat may be used, but a cross-linking acid catalyst is preferred.
• a sulfonic acid compound or a carboxylic acid compound may be used, and, as the compound capable of generating acid due to heat, a thermal acid generator may be used.
• sulfonic acid compounds or carboxylic acid compounds include p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium trifluoromethanesulfonate, pyridinium p-toluenesulfonate, pyridinium-4-hydroxybenzenesulfonate, salicylic acid, camphorsulfonic acid, 5-sulfosalicylic acid, 4-chlorobenzenesulfonic acid, 4-phenolsulfonic acid, pyridinium-4-phenolsulfonate, benzenedisulfonic acid, 1-naphthalenesulfonic acid, 4-nitrobenzenesulfonic acid, citric acid, benzoic acid, and hydroxybenzoic acid.
• thermal acid generators examples include K-PURE [registered trademark] CXC-1612, K-PURE CXC-1614, K-PURE TAG-2172, K-PURE TAG-2179, K-PURE TAG-2678, K-PURE TAG2689 (each of which is manufactured by King Industries, Inc.), and SI-45, SI-60, SI-80, SI-100, SI-110, SI-150 (each of which is manufactured by Sanshin Chemical Industry Co., Ltd.).
• cross-linking catalysts may be used each alone or in combination of two or more.
• an amine compound or an ammonium hydroxide compound may be used, and, as the compound capable of generating a base due to heat, urea may be used.
• amine compounds include tertiary amines, such as triethanolamine, tributanolamine, trimethylamine, triethylamine, trinormalpropylamine, triisopropylamine, trinormalbutylamine, tri-tert-butylamine, trinormaloctylamine, triisopropanolamine, phenyldiethanolamine, stearyldiethanolamine, and diazabicyclooctane, and aromatic amines, such as pyridine and 4-dimethylaminopyridine.
• Further examples of amine compounds include primary amines, such as benzylamine and normalbutylamine, and secondary amines, such as diethylamine and dinormalbutylamine. These amine compounds may be used each alone or in combination of two or more.
• ammonium hydroxide compounds include tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, benzyltrimethylammonium hydroxide, benzyltriethylammonium hydroxide, cetyltrimethylammonium hydroxide, phenyltrimethylammonium hydroxide, and phenyltriethylammonium hydroxide.
• the compound capable of generating a base due to heat for example, a compound having a thermally unstable group, such as an amide group, an urethane group, or an aziridine group, so that it generates an amine by heating it, may be used.
• a compound having a thermally unstable group such as an amide group, an urethane group, or an aziridine group
• the compounds capable of generating a base due to heat include urea, benzyltrimethylammonium chloride, benzyltriethylammonium chloride, benzyldimethylphenylammonium chloride, benzyldodecyldimethylammonium chloride, benzyltributylammonium chloride, and choline chloride.
• the amount of the cross-linking catalyst contained generally ranges from 0.0001 to 20% by mass, preferably from 0.01 to 15% by mass, further preferably from 0.1 to 10% by mass based on the total solid content of the protective film forming composition.
• the protective film forming composition of the present invention may contain, as an optional component, a surfactant for improving the application properties with respect to a semiconductor substrate.
• a surfactant for improving the application properties with respect to a semiconductor substrate.
• the surfactants include nonionic surfactants, e.g., polyoxyethylene alkyl ethers, such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, and polyoxyethylene oleyl ether; polyoxyethylene alkyl aryl ethers, such as polyoxyethylene octyl phenyl ether and polyoxyethylene nonyl phenyl ether; polyoxyethylene-polyoxypropylene block copolymers; sorbitan fatty acid esters, such as sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, and sorbitan tristearate; and poly
• surfactants may be used each alone or in combination of two or more.
• the amount of the surfactant contained generally ranges from 0.0001 to 10% by mass, preferably from 0.01 to 5% by mass to the total solid content of the protective film forming composition.
• the protective film forming composition of the present invention generally has a solid content of from 0.1 to 70% by mass, preferably from 0.1 to 60% by mass.
• the solid content indicates a content ratio of the total component remaining after removing the solvent from the protective film forming composition.
• the ratio of the polymer in the solid content is preferably within the range of from 1 to 100% by mass, from 1 to 99.9% by mass, from 50 to 99.9% by mass, from 50 to 95% by mass, and from 50 to 90% by mass, while increasing preference.
• the substrate having a resist pattern according to the present invention may be produced by applying the above-described protective film forming composition onto a semiconductor substrate and baking the applied composition.
• Examples of semiconductor substrates to which the protective film forming composition of the present invention is applied include a silicon wafer, a germanium wafer, and compound semiconductor wafers, such as gallium arsenide, indium phosphide, gallium nitride, indium nitride, and aluminum nitride.
• the inorganic film is formed by, for example, an ALD (atomic layer deposition) method, a CVD (chemical vapor deposition) method, a reactive sputtering method, an ion plating method, a vacuum deposition method, or a spin coating method (spin on glass: SOG).
• ALD atomic layer deposition
• CVD chemical vapor deposition
• a reactive sputtering method a reactive sputtering method
• ion plating method ion plating method
• vacuum deposition method a vacuum deposition method
• spin coating method spin on glass: SOG
• the inorganic films include a polysilicon film, a silicon oxide film, a silicon nitride film, a silicon oxynitride film, a BPSG (Boro-Phospho Silicate Glass) film, a titanium nitride film, a titanium nitride oxide film, a tungsten nitride film, a gallium nitride film, and a gallium arsenide film.
• a polysilicon film a silicon oxide film, a silicon nitride film, a silicon oxynitride film, a BPSG (Boro-Phospho Silicate Glass) film, a titanium nitride film, a titanium nitride oxide film, a tungsten nitride film, a gallium nitride film, and a gallium arsenide film.
• the protective film forming composition of the present invention is applied onto the above-mentioned semiconductor substrate by an appropriate application method, such as a spinner or a coater. Then, the applied composition is baked using a heating means, such as a hotplate, to form a protective film.
• the conditions for baking are appropriately selected from those at a baking temperature from 100 to 400° C. for a baking time from 0.3 to 60 minutes.
• Preferred conditions for baking are those at a baking temperature from 120 to 350° C. for a baking time from 0.5 to 30 minutes, and more preferred conditions are those at a baking temperature from 150 to 300° C. for a baking time from 0.8 to 10 minutes.
• the thickness of the formed protective film ranges, for example, from 0.001 to 10 preferably from 0.002 to 1 more preferably from 0.005 to 0.5
• cross-linking sometimes unsatisfactorily proceeds, making it difficult to obtain a resistance of the formed protective film to a resist solvent or a basic aqueous hydrogen peroxide solution.
• the resultant protective film sometimes undergoes decomposition due to heat.
• Exposure through a mask (reticle) for forming a predetermined pattern is conducted, and, for example, an i-line, a KrF excimer laser, an ArF excimer laser, an EUV (extreme ultraviolet light), or an EB (electron beam) is used.
• an alkaline developer is used, and the conditions are appropriately selected from those at a development temperature from 5 to 50° C. for a development time from 10 to 300 seconds.
• a usable alkaline developer includes, for example, an aqueous solution of an alkali, e.g., an inorganic alkali, such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, or aqueous ammonia; a primary amine, such as ethylamine or n-propylamine; a secondary amine, such as diethylamine or di-n-butylamine; a tertiary amine, such as triethylamine or methyldiethylamine; an alcohol amine, such as dimethylethanolamine or triethanolamine; a quaternary ammonium salt, such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, or choline; or a cyclic amine, such as pyrrole or piperidine.
• an alkali e.g., an inorganic alkali, such as sodium hydroxide,
• aqueous alkali solution to which an alcohol, such as isopropyl alcohol, or a surfactant, such as a nonionic surfactant, is added in an appropriate amount, may also be used.
• a preferred developer is quaternary ammonium salt, and further preferred are tetramethylammonium hydroxide and choline.
• a surfactant may be added to the above developer.
• a method in which development is conducted using an organic solvent, such as butyl acetate, instead of an alkaline developer, to develop a portion with an unimproved alkali dissolution rate of the photoresist, may be used.
• the protective film is subjected to dry etching.
• the surface of the inorganic film is exposed, and, when the inorganic film is not formed on the surface of the semiconductor substrate used, the surface of the semiconductor substrate is exposed.
• the resultant substrate is subjected to wet etching using a wet etching liquid for semiconductor, forming a desired pattern.
• a general chemical liquid for etching a wafer for semiconductor may be used, and, for example, both a substance exhibiting acidic property and a substance exhibiting basic property may be used.
• substances exhibiting acidic property include hydrogen peroxide, hydrofluoric acid, ammonium fluoride, acidic ammonium fluoride, ammonium hydrogenfluoride, buffered hydrofluoric acid, hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, and a mixture thereof.
• substances exhibiting basic property include a basic hydrogen peroxide solution obtained by mixing ammonia, sodium hydroxide, potassium hydroxide, sodium cyanide, potassium cyanide, or an organic amine, such as triethanolamine, with a hydrogen peroxide solution so that the pH of the resultant solution becomes basic.
• a specific example includes SC-1 (ammonia-hydrogen peroxide solution).
• SC-1 ammonia-hydrogen peroxide solution
• the following could be used as a chemical liquid for wet etching: a mixture of a hydrogen peroxide solution and a substance that makes the pH to become basic, for example, urea, so that the heated mixture causes urea to undergo thermal decomposition, generating ammonia, resulting in the pH to eventually become basic.
• These chemical liquids may contain an additive, such as a surfactant.
• the temperature at which the wet etching liquid for semiconductor is used ranges desirably from 25 to 90° C., further desirably from 40 to 80° C.
• the wet etching time ranges desirably from 0.5 to 30 minutes, further desirably from 1 to 20 minutes.
• HLC-8320GPC manufactured by Tosoh Corp.
• GPC Column: Shodex [registered trademark]-Asahipak [registered trademark] (Showa Denko K.K.) Column temperature: 40° C.
• Flow rate 0.35 mL/minute
• Eluent tetrahydrofuran (THF) Standard sample: Polystyrene (Tosoh Corp.)
• the resistance to an acidic hydrogen peroxide solution was evaluated as follows: Each of the protective film forming compositions prepared in Trial Examples 1 to 5 and Comparative Examples 1 to 12, was applied to a 50 nm-thick TiN (Titanium Nitride) deposited substrate, 30 nm-thick TiN (Titanium Nitride) deposited substrate, 30 nm-thick TiON (titanium oxynitride) deposited substrate, or 30 nm-thick WN (tungsten nitride) deposited substrate, and heated at 250° C. for one minute to form a film having a thickness of 110 nm.
• the obtained protective film on each substrate was provided as Examples 1 to 7 and Comparative Examples 1 to 16. Details of each Example and each Comparative Example are provided in Table 1.
• an acidic hydrogen peroxide solution was prepared by mixing 85% phosphoric acid and 30% hydrogen peroxide in a weight ratio of 1:1.
• Each of the deposited substrates applied with the protective film forming composition was immersed for a certain period of time in this acidic hydrogen peroxide solution heated at 60° C. After immersion, the substrate was washed, dried, and by visually checking the condition of the protective film, the period of time required for the protective film to peel off from the substrate was measured.
• the period of time required for the protective film to peel off partially or entirely from the substrate from the time immediately after the immersion of the substrate was defined as the “peeling off time of the protective film”, which is shown in Tables [2-1] to [2-6].
• the protective film forming compositions of Examples showed a longer peeling off time of the protective film to an acidic hydrogen peroxide solution than those of the Comparative Examples in each Table.
• the protective film forming compositions containing a polyvalent carboxylic acid disclosed in the present invention as an additive would demonstrate a better resistance to a wet etching liquid using an acidic hydrogen peroxide solution than the protective film forming compositions not containing the polyvalent carboxylic acid according to the present invention.
• the protective film forming composition containing the polyvalent carboxylic acid as an additive is useful for making a protective film against a wet etching liquid for semiconductor.
• the protective film forming composition of the present invention provides a protective film with excellent resistance when wet etching liquid is applied in processing a substrate and with high dry etching rate, which facilitates substrate processing and demonstrates excellent flattening effect when applied to a stepped substrate.

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